Producing unsaturated terpene hydrocarbons.



ENG-ELBIEBT BERGS, 0F LUDWIGSHAFEN-ON-T'HE-BHINE, GERMANY, ASSIGNOB. T0

BADISCHE ANILIN &: SODA.

FAIBBIK,

MANY, A. CORPORATION.

0F LUDWIGSHAFEN-ON-THE-BHINE, GER- ZE'BODUCING UNSA'ISUMTEEDTEBCPENE HYDBOGABBONB,

Lemme.

No Drawing.

. 7 v V Specification of Letters Patent. Patented M 24 1914,, Application filed December} 1911. Serial Ho. 664,867. v

To all whom it may concern: I,

Be it known that I, Encnnnnnr Bianca, subject of the Ludwigshafen-on-the-Rhine, Germany, have invented new and useful Improvements "in Producing Unsaturated Terpene Hydrocarbons,'of which the following is a specification.

I have found that unsaturated hydrocarbons of the terpene series can be obtained with great ease by treating terpin, or terpin hydrate, era ter ineol, with neutral ofalkaline substances which are capable of splitting 01f water. Such neutral or alkaline substances are, included under the term substance which is free from acid reaction.

. The initial materials can be heatedfeither diterpin.

ferred, before using it,

rectly inan oilebath with the catalytic agent, or be passed,- in the form of vapor, over the catalytic agent which is contained, for instance, in a tube I times, preterable to employ'the vapors in a state of dilution, which can be eifected either by the addition-of air-indifferent gaa'such for exemple-as nitro'gen, or by reducing the piressure undergwhichqthe reaction takes The process of invention is dipentene,

valuable for the production of For the purposes of this invention, terpin hydrate an terpineol are equivalent to The following are examples of how my invention can be carried into practical effect, but the invention not confined to these examples. The parts are by weight.

Example 1: Pass va ore of terpineol, of a boiling point of 218 and a melting point of (3., under reduced pressure, through a tube containing alumina and heated toabout 250 (1., and collect, in a, suitablvessel, the vapors which leave the tube. The oily layer 0 the distillate consists chiefly of dipentTene, a d is separated from the fwater, dried, and fractionally distilled. Instead ofterpineol, terpin, or terpin hydrate, can be' employ When terpin hydrate is employed, it is preto free it as far as possible from water. Further, of

King of-Prussia, residing at in which case it is someemploying aluznina at 250 (3., thorium onid,

or tungsten 02nd, at 200 0. may be used.

Example 2: Pass terpineol vapor, diluted with nitrogen, over alumina at about 250 condense the vapors and wor them up in anyI suitable manner.

xample 3: Pass terpineol vapor over 31111121119. contained in a tube andheated to about 230 C., and condense the resulting vapors and work them up in any suitable m m s. a

Exam le 4:,Allow terpin, which has been 'obtaine by heating' terpin hyd ate, to drop on to alumina heated to from 250 280 (3., while employinga. vacuum, and thenpass the produced vapors over a la heated to about 200 C. Thfixvapors, can be condensed and worked up inany shit-able manner. y 1' I In the foregoing examples, the alumina can be replaced by thorium oxid, or by tungsten dioxid. I'

Now what I claim is 1. The process of producing unsaturated hydrocarbons of the terpene series by heatqmg terpin with a substance which is free from acid reaction which is capableof split-' "ting out water. I

2. The process of producing unsaturated, hydrocarbons oft-the terpene series by passing terpin vapor over heated alumina.

=*3.,The process hydrocarbons of the terpene series by passing terpin, under reduced pressure, over heated alumina. V I I,

4:. The process of producing unsaturated hydrocarbons of the terpene series by pass? ing terpin, under reduced pressure, over heated alumina at a temperatureof about 259" C.

Q In testimonywhereof I have hereunto set myhand in thepresence of two subscribing m as w E i I I ENGELBEE'; BERGrS. Witnesses:

' J. Anne. Lwro,

n. 0. TITI'MANN.

rof alumina (1., while employing ordinary ressure, then of. producing unsaturated 

